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Publication - Professor Jonathan Clayden

    Amino Acid-Derived trans-N-Chloroformylimidazolidinones

    Scalable, Stereoselective Synthesis, Structure, and Utility

    Citation

    Amer, MM, Abas, H, Leonard, DJ, Ward, JW & Clayden, J, 2019, ‘Amino Acid-Derived trans-N-Chloroformylimidazolidinones: Scalable, Stereoselective Synthesis, Structure, and Utility’. Journal of Organic Chemistry, vol 84., pp. 7199-7206

    Abstract

    N-acyl imidazolidinones, which are key intermediates in the stereoselective synthesis of amino acids by "self-regeneration of stereochemistry" methods, are classically made by only moderately diastereoselective methods. We now report that cyclization of pivaldimino-amides with phosgene in the presence of pyridine may be made fully diastereoselective for the trans-N-chloroformylimidazolidinones, and we detail the conformational features of the products. We show that despite the presence of the electrophilic carbamoyl chloride function the products show remarkable stability and may be deprotonated to form enolates with useful reactivity for the synthesis of amino acid derivatives.

    Full details in the University publications repository